PMC:7291971 / 5993-7814
Annnotations
{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/7291971","sourcedb":"PMC","sourceid":"7291971","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7291971","text":"With the aim of enhancing specificity of MTase inhibitors, we developed an approach of bisubstrate inhibitors that display a suitable linker between two adenosines that mimic the transition state of the methyl transfer reaction at 2′-O position of the RNA cap structure [12]. One adenosine is supposed to target the SAM binding site and another adenosine would target the RNA binding site (Fig. 1 ). Recently, we described the synthesis of a first series of bisubstrate adenine dinucleosides with various sulfur-containing linkers [14]. Unexpectedly, such compounds tested at 50 μM or 200 μM concentration failed to inhibit several RNA 2′O-MTases of SARS-CoV, Zika, West Nile, Dengue and Pox viruses such as vaccinia virus. Their potential of inhibition toward N7-MTases of SARS-CoV and vaccinia virus was also explored and none of the S-linked dinucleosides was active against these N7-MTases. From these data, in the present work we replaced the sulfur atom (S) by a nitrogen atom (N) in the linker between both adenosines. This modification presents the advantage of increasing the chemical stability of the linker and offers a possible variability of compounds due to the N-substitution by any chain susceptible to interact with additional protein residues (Scheme 1). It is noteworthy that bisubstrate dinucleosides with N-containing linkers have already been reported in transition state analogs of DNA methylation [15] and of RNA methylation at N6 position of adenosine [16,17]. However, till our work, none viral 2′O-MTase or N7-MTase have been targeted by bisubstrate adenine dinucleosides. This observation led us to explore the impact of N-linkers on the antiviral activity of bisubstrate SAM analogs.\nFig. 1 Rationale for designing a library of bisubstrate compounds for targeting RNA 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